From the funky to the sublime, we have the best spots for putting up your feet and sipping the day away.
Photo: Doug Pearson//Corbis
This lively bar on Jamaica's western tip is a nonstop show—from locals performing aerial acrobatic dives from even higher cliffs, to tourists psyching up to take their own leaps from one of five rocky platforms descending from the bar's clifftop aerie (ignoring red warning signs detailing the risks). Consider bringing some extra cash for offering the local divers a tip. And don't forget to watch for that glorious sunset.
Signature Drink: Grab a local beer, because is there anything better on a hot Jamaican day than a cold bottle of Red Stripe? Rum drinkers go for Rick's Famous Planter's Punch, a sweet, classic blend of rum and fruit juices that is, as the bar menu reminds, "a way of life here, mon."
Stay: Just down the coast, the mood goes from party to romance at The Caves, where 12 thatched-roof cottages dot the limestone cliffs. All-inclusive rates start at $470; 876/957-0270. —Tracey Minkin
Photo: Steve Simonsen
Jost Van Dyke, BVI
Locally brewed beer and Firewater Rum are served with pearls of wisdom from proprietor Foxy himself at this legendary Great Harbour beach bar on Jost Van Dyke, a favorite mingle for yacht passengers, captains, and crew. A sprawling open-air dining room, festooned with t-shirts and other detritus left by prior visitors, speaks to Foxy’s popularity as well as the surprising quality of the food — the tamarind BBQ ribs are excellent. Foxy’s “Old Year’s Night” party is the best New Year’s Eve bash in the Caribbean.
Signature Drink: This bar is so cool, it has two iconic drinks. The Dread Fox pairs Foxy’s own Firewater Rum with lime sour mix and cranberry juice over rocks. The Sly Fox pairs the Firewater Rum with margarita mix and a dash of bitters over ice.
Photo: Courtesy of La Gloriette
St. Barts is rightly known as the ultimate luxury destination in the Caribbean. But sometimes, the greatest luxury is a simple open-air shack overlooking a placid bay, which is what makes La Gloriette such a find. Dotting Le Grande Cul de Sac on the island's northeast shore, this eminently affordable bar couldn't get any simpler: a few tables shaded by sea grape trees and empty, soft sand that stretches out on either side. The best conch fritters on the island just sweeten the deal; 33-59-029-8571.
Signature Drink: La Gloriette bottles its own secret recipe of St. Barts's signature cocktail, the Rhum Vanille, with rum, vanilla, ginger, coconut, and banana. Plan on picking up your own personal bottle (or two) to keep some St. Barts magic on hand.
Stay: The sleek style of Le Sereno is just a short walk up the beach. The enormous suites have dark hardwood flooring and four-poster beds, most with private beachfront porches. Rates start at $775. —Edward Readicker-Henderson
Photo: Courtesy of Bolongo Bay
This beloved St. Thomas hang-out comes with its own killer soundtrack: Live bands perform here just about every day of the year, including Christmas. To channel the local island vibe, get down to the weekly Wednesday Carnival, a spectacle of fire walkers, limbo dancers, and stilt-walking Mocko Jumbies—colorfully coiffed ambassadors of Afro-Caribbean culture who are believed to ward off evil spirits. Locals and tourists alike turn up for the accompanying West Indian buffet and steel-pan bands. The music spills out to a lively beach volleyball court and lounge chairs scattered on the sand, but if you'd rather listen to the surf, it's just a few steps to the shallow, protected waters of Bolongo Bay.
Signature Drink: Cruzan rum is distilled on neighboring St. Croix, and five varieties (dark, coconut, pineapple, banana, and citrus) get poured into the buckets of Iggies's VooDoo Juice, barely tamed by splashes of cranberry and pineapple juices.
Stay: Iggies is just a 10-minute drive by cab ($10) or private transfer ($55 per hour) from the island's premier luxury resort, the serene Ritz-Carlton, St. Thomas, where Caribbean-contemporary rooms and suites open onto views of Great Bay and St. John. Rates start at $339; 340/775-3333.
Photo: Courtesy of Cap Maison, St. Lucia
True story: Fishermen who really did think clothes were too much effort brought their catch into tiny, jungle-lined, and ridiculously scenic Smuggler's Cove to sell. Putting up a bar was kind of a no-brainer from there. Do what St. Lucians do, and take the game of dominoes very, very seriously inside the Naked Fisherman, backed up against a steep hill with a thatched roof that makes it look like it grew there. Or spend the day on a lounger in the sand, tide line at your feet. You can combine the best of outside and inside on the bar's wide balcony while the afternoon turns the sea a hundred shades of jade green.
Signature Drink: Try the mean rum punch, spicier than most in the Caribbean. (St. Lucians like it hot.) Sweet cinnamon and a bitters after-burn mix perfectly with dark rum.
Stay: It’s an easy stroll right up the bluff to Cap Maison, a sophisticated, Mediterranean-inspired boutique hideaway. Rates start at $450. A 90-minute drive to the other side of the island takes you to Jade Mountain’s glorious rooms, which perch you between green mountains and the emerald bay. Rates start at $1,125. —E.R.
Photo: Julien Campeil
Jost Van Dyke, BVI
It looks like a friendly invasion: boatloads of happy revelers spilling off catamarans and dinghies in the direction of the white sand in front of the tiny Soggy Dollar Bar, so named because you have to swim or wade ashore to get your drink. Beach chairs line the shore, so you can sit and stare out to sea or join the crowd, bobbing in the surf while holding a to-go cup high. It's a constant party, and everyone's invited; you can even take a little of the fun home, thanks to a small gift shop on site. The souvenir Painkiller T-shirt tagline: "A sunny drink for shady people." Wear it with pride.
Signature Drink: Like "Semper Fi" unites Marines, the Painkiller unites Caribbean travelers. It's that famous and that good: premium dark rum, pineapple and orange juices, and cream of coconut, topped with freshly grated Grenadian nutmeg.
Stay: The Moorings Yacht Charter Vacations can have you cruising local waters in high Caribbean style, and dropping anchor at Soggy Dollar. Rates start at $3,000 per week; 855/203-5321. Prefer to sleep on land? Nearby Peter Island Resort & Spa runs a day excursion to Soggy Dollar (and the rest of Jost Van Dyke) every Tuesday. Rates start at $500 (excursions are $150 per person, round-trip); 800-895-6097.
—Antonia van der Meer
Photo: Courtesy of Sandbar
Grand Turk Grand Turk may just be the mellowest spot in the laid-back Caribbean, maybe even on Earth. Not much moves but the wild horses that roam the beaches and streets. But come evening, the Sandbar fills to overflowing. People who've been hanging out since lunch slide over at the teak tables to make room for the evening crowd, yet nobody leaves this simple wooden platform directly above the beach. The "green flash" seems to appear on command each night, and on Fridays, you can hear the rake 'n' scrape band playing across the street.
Signature Drink: The Rum Punch matches the Caribbean standard—rum, juice, bitters—with a marvelous level of mango that hides just how potent the drink really is.
Stay: Across the street, Manta House's beach-view bungalows with one, two, or three bed-rooms start at $1,100 per week. The Osprey Beach Hotel has spacious suites and serves the best breakfast on the island. Rates start at $100. —E.R.
Photo: Courtesy of British Virgin Islands Tourist Board
Norman Island, BVI
The naked truth is that while the legendary debauchery at this 100-foot party boat has been slightly tamed—nude diving off the top deck is no longer officially sanctioned for safety reasons, for example—things still get plenty wet, wild, and wiggly as the rum and ski shots flow. Sail into the Norman Island bight and you’ll hear the music fueling a perpetual dance party on the aft deck, broken only by an occasional splash signaling that someone has just earned themselves bragging rights … and maybe a new t-shirt, too.
Signature Drink: Things are simple here on the Willy-T, which means that the signature quaff, of the house gold rum is either drawn from a line-up of shot glasses on a waterski … or perhaps taken from another Caribbean reveler’s body.
Ramshackle doesn’t begin to describe Bomba’s Beach Shack: seemingly thrown together last week from whatever scraps of driftwood happened to bob ashore at Capoon’s Bay, Bomba’s has actually been around for 40 years, making it a bonafide institution among Caribbean beach bars. Bomba himself still holds court each month at the bar’s libertine Full Moon Party, where you’re certain to see more than one “moon” even if you haven’t been indulging in the (possibly hallucinogenic) mushroom tea. The Shack is a bit tamer at other times of the month, when it attracts surfers during the daytime and a mixed crowd of locals and tourist at all hours.
Signature Drink: If you’re daring and lucky enough to come when there’s a supply on hand, try the mushroom tea and see if the tales of its potency are true. The Bomba Rum Punch is a more conventional alternative that will still keep you dancing all night.
Photo: Courtesy of The Island Last Resort
Bellamy Cay, BVI
Only in the British Virgin Islands can you literally go from the airport to a private-island beach bar in less time than it takes to retrieve your luggage. Just exit the Beef Island airport terminal, turn left, walk to Trellis Bay, and call the free launch to take you to tiny Bellamy Cay, home of the Island Last Resort. Enjoy live music every night, munch a tasty Cuban sandwich at the bar, and soak in the island’s pirate history (buccaneer Samuel Bellamy made a fortune by spotting treasure-laden Spanish galleons from here).
Signature Drink: Given the popularity of its Cuban sandwiches, it’s no wonder that the go-to drink here is a handmade mojito.